Bob Dylan, one of the greatest and most influential songwriters of all time, turns 75 on Tuesday. To celebrate his graceful march onward into advanced years, I’ve decided to look back upon his awe-inspiring career and rank each album, from best to worst.
Some key criteria considered for this venture: level of songwriting, lyricism, and instrumentation; critical and commercial success; importance within the context of Dylan’s overall discography; lasting influence on other artists; and general fan consensus based solely on having a finger to the wind of online and print conversations about his career.
This list seeks to be a more honest look at Dylan’s career, as far too many listicles weigh heavily in favor of the ’60s at the expense of subsequent decades, perhaps out of deference to long-standing clichés that Dylan the Protest Folkie and Dylan the Inventor of Modern Rock ‘n’ Roll are the only Dylans who matter. You might be shocked, however, to learn that some of Dylan’s best work occurred when he was well over the hill and his original Boomer fanbase had become grandparents.
But because no two Bob Dylan fans ever fully agree on Bob Dylan, I understand the vein-bursting rage some of you may experience upon reading this list. Feel free to start a discussion with me on social media, as there’s probably nothing I’d enjoy more. Especially if your message is in all-caps and seething with hate.
And, on that note, let's get started:
37. Christmas in the Heart (2009)
Look, the music here isn’t bad, per se. In fact, it’s mildly refreshing to hear a 68-year-old Dylan goof around for 42 minutes of unabashed yuletide joy (you can thank this record for the bizarro “Must Be Santa” music video). But, call me a grinch, this record is just downright inessential—even in December.
Essential track(s): “Must Be Santa,” if only for the chuckles.
36. Dylan (1973)
Dylan seemingly foresaw that this would be the most widely panned album of his career: He fought against its release. The collection of Self Portrait outtakes (tells you all you need to know) featured no original songs and is flat-out unlistenable.
Essential track(s): “Spanish Is the Loving Tongue,” if only to understand how truly magnificent the piano-centric version released a few years earlier as a b-side to "Watching the River Flow" was by comparison.
35. Down in the Groove (1988)
Not even a pair of lyrical collaborations with Grateful Dead lyricist Robert Hunter could save this easy-breezy, boring-as-hell trainwreck. Be thankful, however: This record launched Dylan’s “Never Ending Tour” and gave us “Death Is Not the End,” which Nick Cave and friends beautifully interpreted a decade later.
Essential track(s): “Death Is Not the End” and “Silvio,” the Dylan-Hunter collabo that found new life as a live song.
34. Under the Red Sky (1990)
The conceptual dissonance is remarkable here. For an album largely based on nursery rhymes and gobbledygook, producer Don Was brought in a serious roster of heavy hitters for studio collaborations: Elton John, George Harrison, Slash, Stevie Ray Vaughan, among others. The result: too much of absolutely nothing. Dylan himself has admitted as much.
Essential track(s): “Born in Time,” which was a castaway from the year prior’s far superior record.
33. Saved (1980)
Oddly enough, the most overtly religious record in Dylan’s evangelical trilogy is one of the most dispassionate-sounding records in his discography. And it suffers from a lack of Mark Knopfler, who made Dylan’s previous foray into gospel a blissful experience (see Slow Train Coming).
Essential track(s): “Pressing On,” because it’s a beautiful gospel song and an epic set-closing live rendition was the saving grace (pun possibly intended) of his ill-fated 1980 tour.
32. Knocked Out Loaded (1986)
Rushed, unfocused, and unengaging—this record would’ve benefited from a few second thoughts before release. The only reason it’s not among the five worst albums on this list, however: the 11-minute epic narrative “Brownsville Girl,” one of Dylan’s most sorely underrated classics.
Essential track(s): Co-written with playwright/actor Sam Shepard, “Brownsville” is a tragicomical ode to Western cinema with one of the most transcendent choruses in Dylan’s catalog.
31. Self Portrait (1970)
“What is this shit?” Rolling Stone’s Greil Marcus famously proclaimed upon hearing this double-disc collection of songs Dylan cobbled together with the express purpose of pissing off the hippies who expected the world of him. “I wish these people would just forget about me. I wanna do something they can’t possibly like,” he later revealed of his thinking behind the puzzling release. In 2013, we learned these sessions actually weren’t all bad: Another Self Portrait, which features alternate takes and outtakes from the time, is among the greatest installments in The Bootleg Series.
Essential track(s): “Wigwam,” which made a glorious cameo in The Royal Tenenbaums, and the lovely “Alberta #2.”
30. Good as I Been to You (1992)
The first full album of just Dylan, a harmonica, and an acoustic guitar in nearly three decades. No original songs here, just folk traditionals that feel enchantingly familiar and demonstrate Dylan’s eternal position as professor emeritus of the folk tradition.
Essential track(s): “Frankie and Albert” and “Froggie Went a-Courtin’,” which coincidentally included Dylan’s froggiest vocal performance to date.
29. Fallen Angels (2016)
Released only a week ago, the second installment of Dylan’s “Great American Songbook” albums is quite good—his world-weary septuagenarian croon is stellar; the arrangements are beautiful; and the performances are tight. But it’s too close in sound and concept to its predecessor (see Shadows in the Night), and only serves to make Dylan fans pace even more impatiently for the next set of originals.
Essential track(s): “Melancholy Mood,” “Young at Heart.”
28. Empire Burlesque (1985)
This is the sound of Dylan misguidedly attempting to get hip with the times—a dated album heavy on synths and low on shelf life. By recruiting famed post-disco producer Arthur Baker to lend some slick dance-club instrumentation, Dylan ended up obscuring some truly wonderful songwriting. As an Empire track, “When the Night Comes Falling From the Sky” is a cluttered mess; but as we heard on The Bootleg Series, an arena-sized outtake rendition featuring members of the E Street Band is a lost gem.
Essential track(s): “Dark Eyes,” Dylan’s best acoustic song in a decade; and “Tight Connection to My Heart,” especially for its incredibly awkward music video.
27. Shadows in the Night (2015)
Like Fallen Angels, the inaugural record in Dylan’s tribute to Tin Pan Alley is a wonderful showcase of the rock legend’s passion for performing and interpreting. Its emotionally complex, slightly darker tone puts it ahead of its successor, however.
Essential track(s): “Full Moon and Empty Arms” and “That Lucky Old Sun.”
26. Bob Dylan (1962)
The record that started it all. The critical and commercial response was negligible at the time, but Dylan’s self-titled debut provides a clear blueprint for his subsequent folk classics. This is an early glimpse of his gift for emotive strumming and myth-making abilities to adapt traditional melodies into brand-new forms.
Essential track(s): “Man of Constant Sorrow” and “Baby, Let Me Follow You Down,” which later became a barnstorming live staple of his mythical 1966 world tour with The Hawks.
25. Shot of Love (1981)
The final entry in Dylan’s Christian trilogy is worth it for two songs alone: “Lenny Bruce,” a piano ballad ode to the late counterculture comedian of the same name; and “Every Grain of Sand,” the heartwrenchingly powerful song about life, love, faith, and death. Emmylou Harris and Sheryl Crow performed it at Johnny Cash’s funeral and, full disclosure, this very writer has told his wife on numerous occasions he wants the same song to send him off.
Essential track(s): “Every Grain of Sand,” “Lenny Bruce,” and “The Groom’s Still Waiting at the Altar,” an explosive allegorical rocker that was added to the album upon CD release.
24. Tempest (2012)
Late-career Dylan continued to find his creative stride with this 10-song set of literary songs (including the title track, a 14-minute ballad about the Titanic) that artfully melded the pre-rock, folk, and blues he explored on prior records. Bleak yet witty and acerbic, Dylan yet again proved himself a masterful storyteller.
Essential track(s): “Duquesne Whistle,” co-written with Robert Hunter; and “Pay in Blood.”
23. World Gone Wrong (1993)
Dylan followed up the moderately successful Good as I Been to You with yet another all-acoustic record. The darker, more focused effort earned him a Grammy along with greater critical and musical success than its predecessor, officially putting the uneven ’80s behind him.
Essential track(s): “World Gone Wrong” and “Blood in My Eyes” reminded everyone of the Dark Side of Bob Dylan.
22. Pat Garrett & Billy the Kid (1973)
This soundtrack to Sam Peckinpah’s classic Western—in which Dylan appeared as a cowboy named Alias—largely consists of instrumentals not worth revisiting. It does, however, earn its keep with four versions of theme song “Billy” and, of course, “Knockin’ on Heaven’s Door.”
Essential track(s): “Knockin’ on Heaven’s Door,” for its simplistic beauty and a reminder of what a great composition it was before Axl Rose and his “hey hey hey” ad-lib nearly ruined it.
21. Together Through Life (2009)
Dylan’s attempt at a full album of songs co-written with Robert Hunter went much more successfully than the lyricists’ previous collaborations. Never before had Dylan sounded so pissed off and disappointed than on this grunge-blues collection of road songs.
Essential track(s): “Jolene” and “Beyond Here Lies Nothin,’” which soundtracked a music video featuring Tarantino levels of graphic violence.
20. Planet Waves (1974)
The gang’s all here. One year before officially releasing the legendary late ’60s Basement Tapes, Dylan and The Band reunited to record this ramshackle comeback record, complete with accordions, organs, and screwball Americana influences. Now firmly entrenched in fatherhood, Dylan here birthed one of his most timeless classics: “Forever Young.”
Essential track(s): “Forever Young,” “On a Night Like This,” and “Hazel,” which makes a riveting appearance during Dylan’s set on The Last Waltz.
19. Slow Train Coming (1979)
Dylan’s seemingly abrupt foray into born-again Christianity left many fans alienated. But with help from Mark Knopfler’s creamy guitar licks and some horns provided by Muscle Shoals—where the album was recorded—Dylan’s fiery exploration of faith and unbelievers became viewed as one of his richest works as the initial disappointment wore off.
Essential track(s): “Gotta Serve Somebody” and “Precious Angel,” which features Knopfler guitar work so sublime you’ll want to praise the Lord even if you don’t believe in one.
18. The Times They Are a-Changin' (1964)
His first album of entirely original compositions, this is what many think of when they think of musical social commentary. Eschewing any sense of subtlety, Dylan wrote straightforward protest songs, attacking institutional racism (“Only a Pawn in Their Game”), nationalism and the warfare state (“With God on Our Side”), and fuddy-duddies who stood in the way of social change (the classic title track). A year later, he abandoned protest music altogether. Try as they might, however, no one else has made overtly political music quite like this.
Essential track(s): The aforementioned songs.
17. Street-Legal (1978)
Ignore the harsh reviews that accompanied this soulful outing’s initial release—this is a damn good record and would be higher up the list if this writer’s personal preferences weighted more heavily. A little funky, a little jazzy, and loaded with dense lyrics about sex, love, and the apocalypse, the unusual (for Dylan) album fell prey to muddied production. Two decades later, it got a proper remaster—the saxophone and back-up soul singers now sound clearer, etc.—and became a critical favorite upon second glance.
Essential track(s): “Changing of the Guards,” with its mercurial chord progression; and climactic album closer “Where Are You Tonight? (Journey Through Dark Heat).”
16. The Basement Tapes (1975)
Perhaps no other album on this list is as hotly debated and discussed as The Basement Tapes. Recorded in 1967 in the basement of the famed Big Pink house in Saugerties, N.Y., this is the sound of post-motorcycle accident Dylan and The Band letting their guards down and just having fun. The mythical sessions were widely bootlegged and produced songs that became hits for The Band, The Byrds, and Manfred Mann, but the official release in 1975 was hurt by overdubs, additional Band-only tracks, and the omission of classics like “I Shall Be Released” and “Quinn the Eskimo (The Mighty Quinn).” Four decades later we got the mammoth Bootleg Series Vol. 11: The Basement Tapes Complete, which proved just how important these sessions were for the history of American songwriting.
Essential track(s): “You Ain’t Goin’ Nowhere,” “Crash on the Levee (Down in the Flood),” and “This Wheel’s on Fire.”
15. Nashville Skyline (1969)
While the rest of his peers rioted at the 1968 DNC, marched on Washington, and experimented with drugs, a domesticated Dylan went to Nashville and immersed himself completely in country music. He recorded with Johnny Cash and dropped the nasal snarl of previous records in favor of a smooth country croon. Some say this album birthed country-rock, though that honor really goes to Gram Parsons and The Byrds a year earlier—which, lo and behold, was indebted to the then-unreleased Basement Tapes. No, the circle won’t be broken.
Essential track(s): “Lay Lady Lay,” “Tonight I'll Be Staying Here with You,” and “I Threw It All Away.”
14. New Morning (1970)
Released four months after Self Portrait but recorded before it, New Morning was, indeed, a new morning for Dylan. Critics hailed the blissed-out songwriting and the return of Dylan’s wry howl. The tumultuous sessions, which included appearances from George Harrison, also produced one of Dylan’s most lasting love songs, “If Not for You,” a sentimental treat that gleams with joy.
Essential track(s): “New Morning,” “If Not for You,” and “The Man in Me,” which achieved cinematic perfection in The Big Lebowski’s opening credits.
13. Modern Times (2006)
With rumbling rockabilly, coming-off-the-rails blues, and grungy use of jazz chords, Dylan packs a wallop here, sounding feisty and ready to kick some ass. The lyrics borrow heavily from classic poetry, folk traditionals, and ’40s balladry—spawning allegations of plagiarism—and Dylan comes off sounding like a prophetic soothsayer with a low, inaudible rumble of doom throughout the record. Bonus points for the head-scratching lyrical shout-out to Alicia Keys.
Essential track(s): “Thunder on the Mountain,” “Someday Baby,” “Ain’t Talkin’,” and the Crosby-esque “When the Deal Goes Down,” which had a Kodachrome music video featuring the lovely Scarlett Johansson.
12. Infidels (1983)
Dylan’s return to secular music was via this dizzying, hard-rocking album, in which the bard careens between themes of the apocalypse, environmentalism, Zionism, and protectionism over post-punk sonic textures (with the occasional reggae funk sprinkled in). The only thing holding back this record from masterpiece status is the puzzling omission of “Foot of Pride” and, more notably, “Blind Willie McTell,” widely considered one of his greatest songs.
Essential track(s): “Jokerman,” “License to Kill,” and “Man of Peace.”
11. Love and Theft (2001)
The second album of his latter-day “renaissance” period buzzes with the sounds of the South, leaning heavily on Harry Smith’s famed folklore, Delta blues mythology, the ambience of a sweaty juke joint, and a Fogerty-like appreciation of all things swampy. Dylan draws from the region’s cultural heritage to tell tales of death, racism, and twisted love; or to just show off his wicked sense of humor.
Essential tracks: “High Water (For Charley Patton),” “Lonesome Day Blues,” and “Mississippi.”
10. Desire (1976)
This is the album that served as the basis for Dylan’s ramshackle Rolling Thunder Revue tour, during which he donned white face-paint and a large fedora and set out on the road with a caravan of like-minded collaborators. Scarlet Rivera’s piercing gypsy-folk violin, a hefty dose of tambourine-and-snare snaps, and Dylan’s melismatic vocals accompany towering allegories, epic adventures, and some (misguided) historical revisionism for what we’ve described as his “sloppiest masterpiece.”
Essential track(s): “Isis,” “Hurricane,” “Oh, Sister.”
9. Another Side of Bob Dylan (1964)
In a single overnight recording session, Dylan emptied several bottles of Beaujolais and laid down this entire record. Or so the legend goes. His first post-“protest music” album, Another Side indeed showcases another side of the musician—one that was annoyed by the preening protest-folk movement and more concerned with existential crises. Here the world was introduced to Dylan as a symbolist poet of the road, a Rimbaud-meets-Kerouac, if you will. The cover might as well have featured Dylan on a motorcycle.
Essential track(s): “Chimes of Freedom,” “My Back Pages,” “It Ain’t Me Babe.”
8. Oh Mercy (1989)
After a string of severe disappointments, Dylan teamed up with legendary producer Daniel Lanois, at the behest of Bono, to create this atmospheric, deeply emotive, and triumphant comeback. Alternating between despair and great hope, it’s the perfect album for a late-night drive on a pitch-black highway—especially after some undescribed biblical event. With the exception of the following year’s record (Under the Red Sky), the wandering bard has been on a hot streak ever since.
Essential track(s): “Ring Them Bells,” “Man in the Long Black Coat,” and “Shooting Star.”
7. The Freewheelin’ Bob Dylan (1963)
Half a century later, this album remains a truly staggering achievement. After being introduced to the civil rights movement by girlfriend Suze Rotolo (pictured on the cover with him), Dylan incorporated the language of social change into his sardonic songwriting, cementing his early-’60s legacy as the quintessential folk troubadour and “voice of a generation”—whether or not he liked it.
Essential tracks: “A Hard Rain’s a-Gonna Fall,” “Don’t Think Twice, It’s All Right,” “Girl from the North Country,” and “Masters of War.”
6. John Wesley Harding (1967)
One might argue that this—not Sweetheart of the Rodeo or Nashville Skyline—is the beginning of alt-country music. While his peers turned to psychedelia, Dylan defiantly turned to rustic, pastoral imagery, relaying allegories and tales seemingly ripped out of Western pulps and outlaw fan-fiction. The songwriting is crisp and the instrumentation is tight, with Dylan employing a startlingly efficient economy of words—every line means something and isn’t just poetic stream-of-consciousness. He barely promoted the album upon its release, perhaps contributing to its underappreciated status, but make no mistake: This is a folk-rock masterpiece.
Essential tracks: “I Dreamed I Saw St. Augustine,” “All Along the Watchtower,” “The Wicked Messenger.”
5. Bringing It All Back Home (1965)
You’ve heard the cliché a million times: This is where Dylan “went electric.” And, yes, this is where he went electric. But lost in that stock phrase is that he did so in an incredibly dramatic fashion. One minute he was an acoustic folk icon, the next he was churning out fiery rock ‘n’ roll with stream-of-consciousness lyrics about the futility of politics and the absurdities of the protest movement that previously (and erroneously) thought it owned him. This sounded unlike anything Dylan had ever made, even the second-disc acoustic half with its surrealist paranoia.
Essential tracks: “Subterranean Homesick Blues,” “Maggie’s Farm,” and “It’s Alright, Ma (I’m Only Bleeding).”
4. Time Out of Mind (1997)
A reminder that Dylan’s best output isn’t limited to the 1960s. This late-’90s tour de force kicked off his so-called renaissance period with a world-weary, plaintive look at mortality and lost love. Dylan reunited with Lanois here for a bleary blues sound, heavy on organs, pedal steel, and echo-drenched vocals—and the result was a Grammy-winning comeback that will likely be remembered as the defining record of Dylan’s late career.
Essential tracks: “Love Sick,” “Not Dark Yet,” “Cold Irons Bound,” and the oft-covered love song “Make You Feel My Love.”
3. Blonde on Blonde (1966)
Visionary in countless ways—among them: one of the first double albums in rock history; epic in length and emotional scope at a time when classic rock was first learning to walk; and an explosive combo of precise Nashville studio-musician instrumentation and Dylan’s bohemian Greenwich Village sensibilities. Our hero uses words as music, twisting and turning them into juggernaut phrases, while the rock ‘n’ roll backing sizzles with energy he—or countless others—has yet to match again.
Essential tracks: “Visions of Johanna,” “Just Like a Woman,” “Rainy Day Women #12 & 35,” and “Stuck Inside of Mobile with the Memphis Blues Again.”
2. Highway 61 Revisited (1965)
It opens with a “snare shot that sounded like somebody’d kicked open the door to your mind,” as Bruce Springsteen described it. And for many other music lovers throughout the last 50 years, that eye-opening rock ‘n’ roll baptism has occurred in similar fashion. No song has had as significant an impact on rock music as “Like a Rolling Stone”—and that’s just the first track on the album. It’s breathtaking, really, how many post-apocalyptic landmarks Dylan crammed into one album (see below). He hisses and scowls like a wild animal, his poetry is combustible and unpredictable. Clichés be damned, this is the sound of Dylan becoming the deity of rock.
Essential tracks: “Like a Rolling Stone,” “Ballad of a Thin Man,” “Highway 61 Revisited,” and “Desolation Row.”
1. Blood on the Tracks (1975)
For the first 15 years of his career, Dylan hid his pain behind verbose sarcasm, surrealist poetry, and folksy tall tales and allegories. And then came the collapse of his nine-year marriage to Sara Lownds—the catalyst for a record of anguished, soul-baring tunes that practically invented the modern confessional singer-songwriter.
Dylan didn’t quite understand why the album resonated so deeply with his fans—“A lot of people tell me they enjoy that album,” he once said. “It’s hard for me to relate to that, you know? I mean, people enjoying that type of pain.” But it’s apparent upon just one listen that by mixing scathing indignation, tenderness, and wistfulness, Dylan perfected the art of looking back on love gone wrong from every possible vantage point.
Yes, Bob, human beings can relate to that.
What’s even more astounding: Dylan essentially recorded the entire album twice—once in New York and then, at the behest of his brother, again in Minneapolis. The finished product took all five Minnesota renditions along with five of the NYC takes. But as its own widely bootlegged product, the entire New York acetate version of Blood on the Tracks (hear a sample below) stands alongside the official release as one of Dylan’s crowning achievements.
Essential track(s): “Idiot Wind,” “Tangled Up in Blue,” “Shelter from the Storm,” and “Simple Twist of Fate.”